Caribbean yacht charters

Sailing experience level

Sailing in the Caribbean

A Caribbean sailing vacation helps you realize your nautical dreams in the most unique way. Each colonized by a different European nation, the Caribbean islands invite you to discover their distinct history and culture. Explore seven island bases, with each offering up a taste of mouthwatering cuisine and exciting things to do. Whether you want calm, protected waters and short island hops or exhilarating blue water passages, we offer a sailing vacation to pique your interest.

More than 700 islands, reefs and cays, make the Caribbean a picture-perfect paradise for sailors at any level. Enjoy easy line-of-sight navigation while island-hopping from one charming harbor to the next aboard your own monohull or catamaran Caribbean charter.

Caribbean Island-Hopping Voyages

Take your vacation to new levels when you set sail for any one of these Caribbean gems:

British Virgin Islands

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1
Explore British Virgin Islands

St. Martin

  • Blue water and coastal sailing
  • World-class diving and snorkeling
  • Glamorous resorts and laid-back beaches
Experience level 2-3
Explore St. Martin

Sailing Antigua

  • Excellent wreck and reef diving
  • Blue water sailing in steady trade winds
  • A stunning beach for each day of the year
Experience level 2
Explore Sailing Antigua


  • Sheltered sailing within a barrier reef
  • Consistent coastal trade winds to exploit
  • Incredible rainforests and Mayan ruins
Experience level 3 ICC RYA
Explore Belize


  • Exciting blue water sailing
  • Warm, yearlong trade winds
  • Excellent diving and snorkeling
Experience level 3
Explore Grenada
St. Lucia

St. Lucia

  • Year-round trade winds
  • Unique, delicious local cuisine
  • Stunning mountainous, rainforest isle
Experience level 3
Explore St. Lucia

Private or group Caribbean sailing adventures

Select from a diverse fleet of catamarans and monohulls that deliver both comfort and performance in a wide range of sizes. Our custom yachts have plenty of space for you and your guests. Whether you take the helm yourself or hire a licensed Sunsail skipper, there’s no better place than the Caribbean to harness the wind and reconnect with the world.

Follow our suggested itinerary, create your own wind-drawn passage or indulge in the ultimate group getaway with a Caribbean flotilla vacation. Come aboard and feel the thrill of a sun-soaked seafaring adventure!

Caribbean bareboat charter vacations

From the romantic and welcoming shores of St. Lucia to the world-famous dive sites of the Bahamas, set sail on a bareboat charter in the Caribbean and you’ll have your choice of marinas, anchorages, and moorings in locations that suit your individual taste. You’ll find a spectacular balance of easy line-of-sight sailing and adventurous open water thrills for that perfect sailing vacation where whatever you say goes.

Caribbean flotilla vacations

The most social way of sailing, a Caribbean flotilla vacation lets you spend your days dropping anchor amid the magical cays, bays, and harbors, while your evenings can be spent with your flotilla sailing companions over dinner or drinking rum punch on the deck of your yacht.

Skippered Caribbean charter vacations

Brush up on your sailing skills or simply let your skipper be your guide, a skippered charter vacation in the Caribbean lets you have the best of both worlds. From the 365 beaches of Antiqua to the European flavor of St. Martin, your qualified skipper will show you the spectacular sights of the Caribbean at the pace you choose.